diff --git a/lib/winston/transports/file.js b/lib/winston/transports/file.js
index 2a8749b39..cef3e0e7d 100644
--- a/lib/winston/transports/file.js
+++ b/lib/winston/transports/file.js
@@ -76,6 +76,7 @@ var File = exports.File = function (options) {
   this.label       = options.label       || null;
   this.timestamp   = options.timestamp != null ? options.timestamp : true;
   this.eol         = options.eol || '\n';
+  this.tailable    = options.tailable    || false;
   this.depth       = options.depth       || null;
   this.showLevel   = options.showLevel === undefined ? true : options.showLevel;
 
@@ -505,32 +506,18 @@ File.prototype._createStream = function () {
 // in the case that log filesizes are being capped.
 //
 File.prototype._getFile = function (inc) {
-  var self = this,
-      ext = path.extname(this._basename),
-      basename = path.basename(this._basename, ext),
-      remaining;
+  var ext = path.extname(this._basename),
+      basename = path.basename(this._basename, ext);
 
   if (inc) {
-    //
-    // Increment the number of files created or
-    // checked by this instance.
-    //
-    // Check for maxFiles option and delete file
-    if (this.maxFiles && (this._created >= (this.maxFiles - 1))) {
-      remaining = this._created - (this.maxFiles - 1);
-      try {
-        if (remaining === 0) {
-          fs.unlinkSync(path.join(this.dirname, basename + ext));
-        }
-        else {
-          fs.unlinkSync(path.join(this.dirname, basename + remaining + ext));
-        }
-      } catch (e) {
-        // If the file was already removed
-      }
+    if (!this.tailable) {
+      this._checkMaxFilesIncrementing(ext, basename);
+      this._created += 1;
+    }
+    else {
+      this._checkMaxFilesTailable(ext, basename);
+      return basename + ext;
     }
-
-    this._created += 1;
   }
 
   return this._created
@@ -538,6 +525,50 @@ File.prototype._getFile = function (inc) {
     : basename + ext;
 };
 
+//
+// ### @private function _checkMaxFilesIncrementing ()
+// Increment the number of files created or
+// checked by this instance.
+//
+File.prototype._checkMaxFilesIncrementing = function (ext, basename) {
+  var remaining;
+
+  // Check for maxFiles option and delete file
+  if (this.maxFiles && (this._created >= (this.maxFiles - 1))) {
+    remaining = this._created - (this.maxFiles - 1);
+    if (remaining === 0) {
+      fs.unlinkSync(path.join(this.dirname, basename + ext));
+    }
+    else {
+      fs.unlinkSync(path.join(this.dirname, basename + remaining + ext));
+    }
+  }
+};
+
+//
+// ### @private function _checkMaxFilesTailable ()
+//
+// Roll files forward based on integer, up to maxFiles.
+// e.g. if base if file.log and it becomes oversized, roll
+//    to file1.log, and allow file.log to be re-used. If
+//    file is oversized again, roll file1.log to file2.log,
+//    roll file.log to file1.log, and so on.
+File.prototype._checkMaxFilesTailable = function (ext, basename) {
+  var tmppath;
+
+  if (!this.maxFiles)
+    return;
+
+  for (var x = this.maxFiles - 1; x > 0; x--) {
+    tmppath = path.join(this.dirname, basename + (x - 1) + ext);
+    if (fs.existsSync(tmppath)) {
+      fs.renameSync(tmppath, path.join(this.dirname, basename + x + ext));
+    }
+  }
+
+  fs.renameSync(path.join(this.dirname, basename + ext), path.join(this.dirname, basename + 1 + ext));
+};
+
 //
 // ### @private function _lazyDrain ()
 // Lazily attempts to emit the `logged` event when `this.stream` has
diff --git a/test/transports/file-tailrolling-test.js b/test/transports/file-tailrolling-test.js
new file mode 100644
index 000000000..199afcaf1
--- /dev/null
+++ b/test/transports/file-tailrolling-test.js
@@ -0,0 +1,92 @@
+var assert = require('assert'),
+    fs = require('fs'),
+    path = require('path'),
+    vows = require('vows'),
+    winston = require('../../lib/winston'),
+    helpers = require('../helpers');
+
+var maxfilesTransport = new winston.transports.File({
+  timestamp: false,
+  json: false,
+  filename: path.join(__dirname, '..', 'fixtures', 'logs', 'testtailrollingfiles.log'),
+  maxsize: 4096,
+  maxFiles: 3,
+  tailable: true
+});
+
+process.on('uncaughtException', function (err) {
+  console.log('caught exception');
+  console.log(err);
+});
+
+vows.describe('winston/transports/file/tailrolling').addBatch({
+  "An instance of the File Transport": {
+    "when delete old test files": {
+      topic: function () {
+        var logs = path.join(__dirname, '..', 'fixtures', 'logs');
+        fs.readdirSync(logs).forEach(function (file) {
+          if (~file.indexOf('testtailrollingfiles')) {
+            fs.unlinkSync(path.join(logs, file));
+          }
+        });
+
+        this.callback();
+      },
+      "and when passed more files than the maxFiles": {
+        topic: function () {
+          var that = this,
+              created = 0;
+
+          function data(ch) {
+            return new Array(1018).join(String.fromCharCode(65 + ch));
+          };
+
+          function logKbytes(kbytes, txt) {
+            //
+            // With no timestamp and at the info level,
+            // winston adds exactly 7 characters:
+            // [info](4)[ :](2)[\n](1)
+            //
+            for (var i = 0; i < kbytes; i++) {
+              maxfilesTransport.log('info', data(txt), null, function () { });
+            }
+          }
+
+          maxfilesTransport.on('logged', function () {
+            if (++created == 4) {
+              return that.callback();
+            }
+
+            logKbytes(4, created);
+          });
+
+          logKbytes(4, created);
+        },
+        "should be 3 log files, base to maxFiles - 1": function () {
+          var file, fullpath;
+          for (var num = 0; num < 4; num++) {
+            file = !num ? 'testtailrollingfiles.log' : 'testtailrollingfiles' + num + '.log';
+            fullpath = path.join(__dirname, '..', 'fixtures', 'logs', file);
+
+            if (num == 3) {
+              return assert.ok(!fs.existsSync(fullpath));
+            }
+
+            assert.ok(fs.existsSync(fullpath));
+          }
+
+          return false;
+        },
+        "should have files in correct order": function () {
+          var file, fullpath, content;
+          ['D', 'C', 'B'].forEach(function (letter, i) {
+            file = !i ? 'testtailrollingfiles.log' : 'testtailrollingfiles' + i + '.log';
+            content = fs.readFileSync(path.join(__dirname, '..', 'fixtures', 'logs', file), 'ascii');
+
+            assert.lengthOf(content.match(new RegExp(letter, 'g')), 4068);
+          });
+        }
+      }
+    }
+  }
+}).export(module);
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